Multi-step reaction with 12 steps
1.1: 75 percent / Dess-Martin periodinane / CH2Cl2 / 3 h / 20 °C
2.1: 96 percent / H2 / Pd/BaSO4 / ethyl acetate / 3 h / 2585.74 Torr
3.1: 85 percent / NaBH4 / methanol / 5 h / -15 - 0 °C
4.1: 95 percent / AcOH / toluene / 5 h / Heating
5.1: LiHMDS / tetrahydrofuran / 0.5 h / -78 °C
5.2: 70 percent / tetrahydrofuran / 0.67 h / -78 °C
6.1: 75 percent / p-toluenesulfonic acid / tetrahydrofuran; H2O / 48 h / 20 °C
7.1: 66 percent / imidazole; 1,1'-(azodicarbonyl)dipiperidine; PMe3 / CH2Cl2; toluene / 24 h / 20 °C
8.1: Me3Al / toluene; CH2Cl2 / 0.25 h
8.2: 88 percent / CH2Cl2; toluene / 45 °C
9.1: TFA / CH2Cl2 / 0.5 h / 20 °C
10.1: 88 mg / PyBOP; iPr2NEt / CH2Cl2 / 3 h / 0 - 20 °C
11.1: TFA / CH2Cl2 / 0.5 h / 20 °C
12.1: 68 percent / PyBOP; iPr2NEt / CH2Cl2 / 4 h / 0 - 20 °C
With
1H-imidazole; sodium tetrahydroborate; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; hydrogen; trimethylaluminum; Dess-Martin periodane; toluene-4-sulfonic acid; acetic acid; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; lithium hexamethyldisilazane; 1,1'-azodicarbonyl-dipiperidine; trimethylphosphane;
Pd-BaSO4;
In
tetrahydrofuran; methanol; dichloromethane; water; ethyl acetate; toluene;
DOI:10.1021/jm060154a